172023-97-1

537039-44-4

172023-97-1

General procedure for the synthesis of 3-bromo-5-(trifluoromethyl)benzyl alcohol from (3-amino-5-(trifluoromethyl)phenyl)methanol: (3-amino-5-(trifluoromethyl)phenyl)methanol (1.6 g, 8.4 mmol) was dissolved in anhydrous acetonitrile (10 mL) and was added slowly and dropwise to a solution of acetonitrile (20 mL) containing copper(II) bromide (2.24 g, 10.0 mmol) and tert-butyl nitrite (1.48 mL, 12.0 mmol) in a solution of acetonitrile (20 mL). The reaction mixture was stirred at 65 °C for 30 min, then cooled to room temperature, poured into 1N hydrochloric acid solution and extracted with ethyl acetate (2×). The organic layers were combined, washed with brine (2×), dried over anhydrous sodium sulfate and concentrated. Purification by silica gel column chromatography (20% ethyl acetate/hexane) afforded the target product 3-bromo-5-(trifluoromethyl)benzyl alcohol (1.48 g, 69% yield).1H-NMR (CDCl3, 500 MHz) δ 7.71 (s, 1H), 7.68 (s, 1H), 7.55 (s, 1H), 4.75 (s, 2H).